35320-23-1Relevant articles and documents
Biochemical and Structural Characterization of an (R)-Selective Transaminase in the Asymmetric Synthesis of Chiral Hydroxy Amines
Li, Fulong,Liang, Youxiang,Wei, Yuwen,Zheng, Yukun,Du, Yan,Yu, Huimin
supporting information, p. 4582 - 4589 (2021/08/07)
An (R)-selective transaminase RbTA with excellent stereoselectivity (>99% ee) in the asymmetric amination of hydroxy ketones was identified. Biochemical characterization showed that RbTA exhibited the highest activity toward 4-hydroxy-2-butanone among reported enzymes, and that it has broad substrate specificity, including for aliphatic, aromatic, and alicyclic ketones. Crystallization of RbTA were performed, as were molecular docking and mutagenesis studies. Residue Tyr125 plays a key role in substrate recognition by forming a hydrogen bond with hydroxy ketone. The applicability of the enzyme was determined in preparative-scale synthesis of (R)-3-amino-1-butanol, demonstrating the potential of RbTA as a green biocatalyst for production of value-added chiral hydroxy amines. This study provides an efficient tool for enzymatic synthesis of chiral hydroxy amines, as well as structural insight into substrate recognition by transaminases in the asymmetric amination of hydroxy ketones. (Figure presented.).
Long-chain piperazine ethyl sulfonamide derivative or medicinal salt thereof and preparation method and application of long-chain piperazine ethyl sulfonamide derivative
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Paragraph 0016, (2016/10/09)
The invention relates to a long-chain piperazine ethyl sulfonamide derivative or medicinal salt thereof and a preparation method and application of the long-chain piperazine ethyl sulfonamide derivative. According to the preparation method, amino acid is reduced with lithium aluminum hydride to obtain alkamine, the amino group is subjected to sulfonylation with prepared sulfonyl chloride, the hydroxide radical is activated with methylsufonyl chloride, the product and a long-chain substituent piperazine compound are subjected to condensation, and then the final product can be prepared. A series of long-chain piperazine ethyl sulfonamide derivatives are synthesized and prepared through the method, the preparation method is simple, raw materials are simple and easy to get, aftertreatment is convenient, the requirement for equipment is low, and industrial production is easy; a preliminary pharmacological experiment indicates that the compound shown as the formula I expresses good antiproliferative activity for a human ovarian cancer cell strain OVCAR-8, a human lung cancer cell strain A549 and a human prostatic caner cell strain PC-3, the cytotoxic activity of the compound is higher than a primer and approximate to positive control Gefitinib and Dasatinib, and it is indicated that the compound is possibly developed into a new antitumor drug.
Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines
Li, Shengkun,Li, Dangdang,Xiao, Taifeng,Zhang, Shasha,Song, Zehua,Ma, Hongyu
, p. 8927 - 8934 (2016/12/07)
Chirality greatly influences the biological and pharmacological properties of a pesticide and will contribute to unnecessary environmental loading and undesired ecological impact. No structure and activity relationship (SAR) of enantiopure succinate dehydrogenase inhibitors (SDHIs) was documented during the structure optimization of boscalids. On the basis of commercial SDHIs, oxazoline natural products, and versatile oxazoline ligands in organic synthesis, the first effort was devoted to explore the chiral SDHIs and the preliminary mechanism thereof. Fine-tuning furnished chiral nicotinamides 4ag as a more promising fungicidal candidate against Rhizoctonia solani, Botrytis cinerea, and Sclerotinia sclerotiorum, with EC50 values of 0.58, 0.42, and 2.10 mg/L, respectively. In vivo bioassay and molecular docking were investigated to explore the potential in practical application and plausible novelty in action mechanism, respectively. The unexpected molecular docking model showed the different chiral effects on the binding site with the amino acid residues. This chiral nicotinamide also featured easy synthesis and cost-efficacy. It will provide a powerful complement to the commercial SDHI fungicides with the introduction of chirality.
HIV INTEGRASE INHIBITORS
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, (2015/09/22)
The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
An easy 'Filter-and-Separate' method for enantioselective separation and chiral sensing of substrates using a biomimetic homochiral polymer
Senthilkumar,Asha
supporting information, p. 8931 - 8934 (2015/05/27)
We present a polyfluorene appended with protected l-glutamic acid that exhibited a reversible α-helix/β-sheet-like conformation and helical porous fibrous morphology mimicking the super-structure of proteins. The new homochiral polymer probe enabled efficient heterogeneous enantioselective separation and chiral sensing of a wide variety of substrates from their aqueous racemic mixture using an easy 'Filter-and-Separate' method.
CARBONITRILE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS
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Page/Page column 148, (2015/12/17)
The present invention relates to a compound of Formula 1, 2 or 3: I II III wherein A is N or -CR0--, where R0 is hydrogen, C1-C6 linear or branched chain alkyl, etc., Z is -CRe --, or, -N--, where Re is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R1 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R2 are independently hydrogen or C1-C6 linear or branched chain alkyl; R3 and R4 are independently hydrogen, C1C6 linear or branched chain alkyl, etc.;. R5 and R6 are independently hydrogen or C1-C6 linear or branched chain alkyl, etc.; R8 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R9 and R10 are independently hydrogen or C1- C6 linear or branched chain alkyl, etc.; Q is --CO--, --(CH2)q--, --(CHRs)q--, or -(CRsRt)q- -, where Rs and Rt are independently C1-C6 linear or branched chain alkyl, aryl, alkylaryl, heteroaryl or alkylheteroaryl; where q is 0, 1, 2, or 3; and, where n is 0, 1, 2, 3, 4 or 5; or, a pharmaceutically acceptable salt thereof, for the treatment of certain diseases, particularly those affected or mediated by the androgen receptor; to compbinations comprising such compounds with a second pharmaceutically active ingredient; to compositions containing such combinations; and to such combinations for the treatment of various diseases, particularly, those affected or mediated by the androgen receptor.
Highly efficient helix-sense-selective polymerization of an achiral phenylacetylene having a bulky group
Qu, Yanqing,Zang, Yu,Zhang, Mingyu,Aoki, Toshiki,Teraguchi, Masahiro,Kaneko, Takashi,Ma, Liqun,Jia, Hongge
supporting information, p. 1777 - 1779 (2016/02/18)
Novel achiral phenylacetylene having a bulky t-butyl group was synthesized and polymerized by a chiral catalytic system containing [Rh(nbd)Cl]2 (nbd: norbornadiene) and chiral amines to yield a one-handed helical polymer having a much higher g value than polymers with no bulky groups. Highly efficient helix-sense-selective polymerization has been achieved using a bulky monomer and a less bulky chiral cocatalyst.
ω-Transaminase-catalyzed kinetic resolution of chiral amines using l-threonine as an amino acceptor precursor
Malik, M. Shaheer,Park, Eul-Soo,Shin, Jong-Shik
supporting information; experimental part, p. 2137 - 2140 (2012/09/25)
Kinetic resolution of chiral amines using l-threonine as a cosubstrate was demonstrated by a biocatalytic strategy in which (S)-selective ω-transaminase (ω-TA) was coupled with threonine deaminase (TD), eliminating the need to use an expensive keto acid as an amino acceptor. The coupled enzyme reaction enabled simultaneous production of enantiopure (R)-amine and l-homoalanine which are pharmaceutically important building blocks. To extend the versatility of this strategy to production of both enantiomers of chiral amines, (R)-selective ω-TA coupled with TD was employed to produce (S)-amine.
Practical convergent laboratory-scale synthesis of a CCR5 receptor antagonist
Crawford, Jason B.,Chen, Gang,Carpenter, Bryon,Wilson, Trevor,Ji, Jenny,Skerlj, Renato T.,Bridger, Gary J.
experimental part, p. 109 - 116 (2012/05/31)
An efficient laboratory-scale synthesis has been developed for the selective CCR5 antagonist 1. The convergent route has a longest linear sequence of nine steps (15 steps overall), and has overall yields of 18-25%. The route has enabled the preparation of 550 g of 1.
Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer
Yuan, Lei,Li, Yanchun,Zou, Chunyang,Wang, Chao,Gao, Jian,Miao, Caixia,Ma, Enlong,Sun, Tiemin
scheme or table, p. 2216 - 2220 (2012/04/18)
In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest.
